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Photochemical and Thermal Cycloaddition Reactions of 3‐Thioxoandrosta‐1,4‐dien‐17‐one with Electron‐Deficient Alkynes
Author(s) -
Möller Stephanie,
Weiß Dieter,
Beckert Rainer
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719971124
Subject(s) - chemistry , cycloaddition , acetylene , dicarboxylic acid , photochemistry , organic chemistry , medicinal chemistry , catalysis
3‐Thioxoandrosta‐1,4‐dien‐17‐one ( 4 ) reacts with acetylene dicarboxylic acid esters to form novel spiro compounds of the thiine type ( 6a, 6b ), whereas with free acids, such as acetylene dicarboxylic acid and propiolic acid, the spirocyclic O,S‐acetals 7a and 7b are obtained. This study demonstrates that the cycloaddition reaction is promoted by photochemical and also thermal activation.